If you are not well prepared and working effectively yourself, here’s what can happen when you bring on board people to help...

You can’t figure out what to ask them to do for you.

You hire the wrong kind of support, and don’t know how to use them.

You aren’t well prepared enough to give them what they need to do their job.

You don’t instruct them well enough and the completed task isn’t what you wanted.

You find you are still a bottleneck, and can’t figure out how to change that.

You end up barely using the support you hire.

It’s no wonder people are risk averse and put off outsourcing in the first place, right?!

But as you already know, no matter how effective and productive you are, there comes a time when the only sustainable way to grow your business is to expand beyond yourself, and grow your team.

Taking Baby Steps To Start

Outsourcing can be HUGELY daunting…

You probably feel that you’re not quite big or busy enough to financially stretch to this.

It still feels easier to just do things yourself; after all it can be frustrating and time-consuming to have to explain to somebody else something that currently only takes you a few minutes to complete.

You’re not quite sure what you need help with; you don’t yet know what you don’t yet know!

It could end up being a huge mistake that costs, not saves you time and money.

What’s interesting is the point at which you should bring on board support often comes way before many people believe they’re ready to, and most people – me included – wait far too long before they do anything about it.

Low Risk Experimentations…

If you’re still at that stage where you think it’s way too soon to get help, there are plenty of small ways you can start…

Pick a designer on Fiverr to create a more professional logo for $5. [Fiverr]

These are relatively cheap and risk-free ways to experience what it’s like to start letting go of the reins so tightly, and see how it feels to have someone else do something for you. I’d encourage you – at whatever stage you’re at – to give some of these a go, if only in the interests of some fun experimentation!

A few words of caution

If you do try any of the above, you may have a bad experience. This does NOT mean that all further experiences of outsourcing will be bad for you, more that you got the wrong person!

Part 2: What To Do BEFORE You Outsource

Despite the risks of outsourcing and not being fully ready to do so, there are numerous things you can do to minimise the potential hassles of working with others.

The following include my recommended MUST DOs if you want a smooth and easy transition, alongside the last section on what to expect as you grow your team…

How To Prep Your Business For Outsourcing

Process Audit

List all the key processes in your business; this is a kind of task audit.

Task List

Keep a list for a week of all the tasks you perform; if you can do it for a month then you’ll have a pretty comprehensive list of the tasks needed to keep your business running.

Put a tick next to each task you feel you shouldn’t be doing and that someone else could do instead of you.

Extra Resource: Try TimeDoctor or Toggl to track what you do and how long it takes you (there’s a free trial/version available for each).

Role Responsibilities & Requirements

When you’ve gained a clearer insight into the tasks you do that could be performed by someone other than you, collate them into related groups (e.g. Marketing, Design, Copywriting, Website admin etc.).

Put together one (or more) role descriptions for the kind of support person you need. You may find it skews heavily towards one particular type of skill – such as a designer or copywriter, or it may be a multi-skilled person (in which case look at a VA/Project Management-type person).

Even if you’re not yet in a position to fill the role, it’s useful to create a Role Description document so that you can be on the lookout for the right person when the time comes.

Clarity in Communication

This is another requirement for you – your communication skills need to be up to scratch if you’re going to be able to communicate effectively what you want help with and what is/isn’t working as you work together.

The vast majority of problems with clients arise because they’re not as clear in their requests as they could be. From missing out bits of information needed (login details, specifics etc.), to mixing up terminology, clarity in your communication with your team is vital.

The following items are useful to include when you work with team mates:

Context and relevant background information

Goals and expectations

Timeframes and deadlines

Any passwords/other data points needed

Links to relevant/contextual resources, templates and documents

Key contacts needed

The more succinct you can be – while still providing a complete picture – the better; otherwise you risk important elements getting lost in paragraphs of waffle

Part 3: What To Expect As You Grow Your Team

Your Role May Change

As your business and team grow, you may find some changes in the role you play in your business…you might spend less time doing the thing you actually do and more time managing and running your business; this is natural unless you specifically set out to build the kind of support team who allow you to do more of what you want to do.

This means that you focus on building a support team to take care of running your business – working ON your business – so that you can spend more time working IN your business. Alternatively, you may be happy to step up and play the CEO role, becoming more of a resource ‘director’ and spokesperson for the business.

Expect The Best, Prepare For The Worst

Before people take on their first contractor/intern/employee they imagine all sorts of awful things happening. Turn this to your advantage and prepare for any/all of these scenarios so you mitigate them should they happen. And then forget about them.

The energy and intention you bring to a relationship with someone working with you in your business sets the tone for the success of it; if you frequently expect the worst of people, they’ll live up (or down) to that expectation.

Instead when you prepare for the worst it, it enables you to expect the best, safe in the knowledge that you’re protected from the worst should it happen.

Summary Actions

Conduct your Process Audit to understand what key processes help you run your business.

Conduct your Technology Audit to identify what tools, platforms and services you use to run your business.

Review the tasks you perform for a week, to identify which could be performed by someone else.

Create a Role Description document for the support role(s) you need.

Prepare yourself and set your expectations for growing your team; the more mentally, emotionally and practically prepared you are, the smoother it will be.

Part 4: How & Where To Find The Right Support

When you’ve prepped your business for outsourcing with ease, how do you expand your team when the time with the right support?

When you’ve got clarity on the kind of support you need, you are in a good position to determine where to look to grow your team.

There are a few options available, including:

Hiring a full- or part-time employee

Engaging a freelancer/contractor

Recruiting an intern/student

They obviously differ in cost and complexity, which is why most people start by engaging a contractor/freelancer, on a one-off basis, ad hoc ongoing basis or on retainer. Your available funds will likely be the biggest factor in determining the right kind of support for you at this stage.

Where To Find Help

There are numerous places to find the support you need. Below I’ve listed a few and added my personal experience, where relevant.

Ad Hoc Service Providers

Fiverr – the beauty of fiverr is naturally the low cost so even if you don’t have the best experience, it’s only cost you $5 which is great for the risk averse.

Much like any freelancer, the key to success on Fiverr is finding a provider you are happy to use again and again. I’ve had limited success here – I’ve hired someone to create social media graphics which were fine but not spectacular and I’ve had clients who had intros and outros for videos created which were solid and professional.

Top tips for a positive experience:

Do a thorough review of their portfolio/work; if you see something similar to what you want, then the chances are higher that you’ll be satisfied. If you don’t, then keep looking, even if the rest of their work looks good.

Read through the testimonials and look for more than just “Good work” comments; look at the Negative Reviews comments (use the filter), and be sure to randomly scroll back through older comments too, not just the latest. Don’t always be put off if a seller has just a handful of negative comments, and do bear in mind the ratio of good to bad comments.

Gramlee – a fast, professional and easy-to-engage service for proofreading and copywriting; I used this a few years ago and was happy with the results (though I had to specify UK English and not US English).

Top tips for a positive experience:

Be selective about how you use these kinds of services; while I wouldn’t use them for a book I’d written (their ‘off the shelf’ service is up to 3k words only), I’m more than happy to use them for blog posts, longer essays and short ebooklets.

If you have specific stylistic requirements, let them know at the top of your document.

99Design Tasks– if you need quick design fixes but not a full-on design service, this is an affordable (from $19) and very speedy (under an hour) option.

Top tips for a positive experience:

Have the right expectations; this service is not about having designs created but tweaks to existing designs. Having said that, if you check out some of their logo tweaks, you might be pleasantly surprised by what can be achieved.

As with any visual task, the more specific you can be in your brief the better; comments like “I know it when I see it” are unhelpful and less likely to get you the results you want. The more information you can provide about your brand guidelines and the look/feel/vibe you want to achieve, the better.

Retainer Service Providers

Fancy Hands – I used Fancy Hands for over a year in 2012/2013. It is a highly affordable service and great for simple tasks, though I found them more effective for life- and admin-oriented versus business-oriented tasks.

Top tips for a positive experience:

One of the best tasks I used them for was to make phone calls; instead of sitting on the phone waiting for someone to pick up or repeatedly trying to get hold of someone, I had them do this for me instead.

You don’t always work with the same assistant so the consistency isn’t always there for certain tasks.

They are very strict about NOT performing lead generation tasks – such as cold calling, researching lists of contacts etc.

Avoid submitting tasks that are too complex e.g. while they can do basic travel research, they’re not great for more complex trips/flight configurations (try Flightfox for that instead).

WP Curve – They come highly recommended by people who use them and are great if you struggle to keep up with the tasks needed to keep your WordPress website running smoothly.

Top tips for a positive experience:

To minimise back and forth and ensure they’ll have everything they need to do their job, always have your login details for key services easily to hand; this includes your login details for:

Your WP website

Your web hosting company

Your domain registration company

If you go for the lowest plan, make sure one of your first tasks is to ask them to install a backup/archive plugin or solution on your site since this isn’t included in their plan 😉

Recruitment Platforms

You have probably heard of, if not already explored, recruitment platforms such as Guru, Upwork (formerly eLance-oDesk) and PeoplePerHour.

Top tips for a positive experience:

Have a clear and concise Role/Task Requirements document, that describes the job/task you want someone to perform.

If you’re looking for someone to support you on an ongoing basis vs. a one-off job, set up a couple of trial tasks as part of your hiring process.

Remember the advice: Be slow to hire and quick to fire; if someone isn’t working out well for you, use the platform’s arbitration process to help, and then move on quickly.

Part 5: How To Prevent Issues With Outsourcing

It can be a daunting experience to start working with someone on your business, when to date it’s been you and you alone…where previously you had full and only creative input, you may now find there are other (professional!) voices and opinions in the mix.

It can be hard to let go and what happens if something actually goes wrong?

It’s important to remember that – assuming you’ve done your hiring job well – the inputs now involved are experienced and professional; it’s YOUR choice to seek input and support. It’s now ok to let go of the reins just a little, to allow the professionals you’ve hired to do their job 😉

You can help yourself to feel more comfortable letting go and trusting by following the practices below to prevent issues from arising in the first place…

Clarity on your ‘why’

Be super clear on what support you need; one of the biggest mistakes I’ve seen clients of my own tech support desk make is assuming we’ll operate in a project manager’s capacity too, when we expressly state that we don’t.

As the CEO and COO of your business, YOU still need to direct operations and ensure you’re the one on-point with the high level overview of what’s happening.

Be aware of the following:

How much project management support do you need vs. pure tech support?

How much strategic advice/input do you need vs. pure implementation?

What kind of response times are you looking for?

How much input into what vs. how do you need?

Communicate your expectations

When you’re clear about your expectations and hopes for your working relationship with a provider, communicate these. We’re not mind-readers and if you have specific expectations of how you want something done, tell us!

Doing this upfront, right at the start of your relationship will help iron out any misunderstanding, miscommunications and mismatched expectations.

Set targets, deadlines and milestones

Never, ever assume that your service provider knows your targets, deadlines and milestones; they may work with numerous clients and while you may have briefly mentioned a specific target/deadline, be explicit and clear about your expectations around this if it’s important and/or business critical.

Failure to communicate and hit deadlines is the #1 cause of most frustrated clients, even though they dropped the ball in communicating the deadline in the first place.

Always keep written records

Even if you communicate by voice (phone/Skype), always keep a written record of your communications. If you do speak, then follow up with a written confirmation of what was spoken about/agreed with an email/other recordable form of text communication.

Try using HipChat or Slack if you need frequent back and forth communication and don’t want to clog up your inbox. communicate.

Have contingency plans and back-ups

No matter how much you trust your service provider(s), always ensure you have a contingency plan in place should your working relationship break down/stop. This means:

Ensuring you always have the latest login details for your key services/tools; use LastPass to manage and share your details securely so no-one but you actually sees your password.

Even if you’re reliant on a particular provider for critical parts of your business, always have a backup option you could turn to if needed in an emergency.

If you stop working with a provider, ensure you revoke and remove ALL their previous accesses.

While you may be lucky and find a crack team you trust, ALWAYS cover yourself should anything not go so smoothly in the future. And if all else fails, revert to your contract – you did sign one, didn’t you? – and see if you can work things out in a professional manner.